Maltodextrin recognition by a macrocyclic synthetic lectin

Stewart, Patrick F. N.; Renney, Charles M.; Mooibroek, Tiddo J.; Ferheen, Sadia; Davis, Anthony P.

doi:10.1039/c8cc05074k

Cited by 28 publications

(18 citation statements)

References 31 publications

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“…Receptors with impressive binding abilities in water were obtained by developing polycyclic cages where parallel aromatic surfaces were connected via water-solubilising spacers. The contribution of hydrophobic interactions from the aromatic units, together with hydrogen bonding established with the spacers, not only allowed the selective recognition of disaccharides such as cellobiose, 102,103 but also more complex targets like maltodextrin 104 and polysaccharides. 105 Other interesting examples of artificial receptors for disaccharides are cyclic peptides obtained from a dynamic combinatorial approach, which showed selectivity for trehalose.…”

Section: Artificial Receptorsmentioning

confidence: 99%

The challenges of glycan recognition with natural and artificial receptors

et al. 2019

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Section: Artificial Receptorsmentioning

confidence: 99%

The challenges of glycan recognition with natural and artificial receptors

et al. 2019

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“…While this optical property was not directly relevant to the present study which focused on the changes in squaraine fluorescence induced by the macrocycle, it does raise the possibility that suitable derivatives of M5 may have future value as a fluorescent host for non-fluorescent guests such as biomedically important saccharides. 23–24…”

Section: Resultsmentioning

confidence: 99%

New tetralactam hosts for squaraine dyes

et al. 2018

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The photophysical properties of a deep-red fluorescent squaraine dye can be improved by encapsulating it within a tetralactam macrocycle. Three new tetralactams are described with different substituents (methyl, methoxy, methylenedioxy) on the macrocycle aromatic sidewalls. The capability of each tetralactam to encapsulate a squaraine dye in chloroform solution was determined experimentally using absorption, fluorescence, and NMR spectroscopy. Two of the tetralactams were found to thread a squaraine dye with association constants on the order of 106 M−1, while a third macrocycle exhibited no squaraine affinity. An X-ray crystal structure of the third tetralactam showed that the substituents sterically blocked squaraine association. Of the two tetralactams that encapsulate a squaraine, one induces an increase in squaraine fluorescence quantum yield, while the other quenches the squaraine fluorescence. The results suggest that these new squaraine binding systems will be useful for biological imaging and diagnostics applications.

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“…Other than recognition of all‐equatorial di‐ and oligosaccharides, only a few examples of effective binding by a biomimetic CBA are reported in the literature. One example has been described by Davis and co‐workers in a recent paper, in which the authors report that receptor 28 selectively binds α‐linked maltodextrins in preference to all‐equatorial substrates . d ‐Maltose, d ‐maltotriose and d ‐maltotetraose were recognised with 1.7 m m ( K a =5.80×10 2 m −1 ), 870 μ m ( K a =1.15×10 3 m −1 ) and 617 μ m ( K a =1.62×10 3 m −1 ) affinities, respectively.…”

Section: Biomimetic Cbas: Design and Affinitiesmentioning

confidence: 94%

Biomimetic Carbohydrate‐Binding Agents (CBAs): Binding Affinities and Biological Activities

Francesconi

Roelens

2019

ChemBioChem

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Mimicking nature in carbohydrate recognition—that is, by using noncovalent interactions exclusively—is a hot topic that has attracted the interest of many scientists in the last 30 years. Carbohydrates are challenging ligands of high biological relevance, playing central roles in several physiological and pathological processes. Carbohydrate‐binding agents (CBAs) of proteic nature, such as lectins, have been extensively used in glycobiology to target carbohydrates, but intrinsic drawbacks conferred on them by their proteic nature limit their therapeutic development. Biomimetic CBAs, artificial small molecules designed for molecular recognition of carbohydrates through noncovalent interactions, have been shown to be effective alternatives in recognising carbohydrates in physiological media, opening the way to biological applications. Herein, we describe the recent achievements in this continually developing field, focusing on those biomimetic CBAs for which biological investigations have been carried out.

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Maltodextrin recognition by a macrocyclic synthetic lectin

Cited by 28 publications

References 31 publications

The challenges of glycan recognition with natural and artificial receptors

The challenges of glycan recognition with natural and artificial receptors

New tetralactam hosts for squaraine dyes

Biomimetic Carbohydrate‐Binding Agents (CBAs): Binding Affinities and Biological Activities

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